Smart Hiring Strategies for Trucking Fleets with Rob Carpenter | Ep 53

Hiring in trucking is one of the biggest challenges fleet owners face, and the wrong decision can be devastating. In this in-depth episode of Miles and Mentors: A Trucking Podcast, Rob Carpenter of Truck Safe returns to share hard-earned lessons about hiring drivers, building reliable fleets, and avoiding the costly mistakes that can ruin a business.

Rob pulls from personal experience, including stories of poor hires that damaged customer relationships and even caused catastrophic financial loss. His insights drive home why hiring cannot be treated as a box-checking exercise but as one of the most important strategic decisions a fleet owner will ever make.

We break down what every trucking company, whether small or scaling, should know about the hiring process. Rob explains why background checks and CDL cards are not enough, and how simple systems like clearinghouse checks, PSP reports, and even a basic road test can reveal major red flags before it is too late. He introduces his “barriers first” approach, a workflow that saves time and money by filtering out unqualified drivers early in the process.

The conversation also highlights the broader impact of hiring. Rob shares how poor driver selection affects more than just operations. It puts a carrier’s reputation, insurance renewals, and long-term survival at risk. He emphasizes that who you put behind the wheel represents your entire company to customers, regulators, and the public.

Beyond hiring, Rob and host Myles dive into other pressing issues in today’s trucking landscape. They discuss the rising cost of equipment, the reliability problems caused by modern emissions systems and electronics, the risks of auto-braking technology, and how artificial intelligence is already changing roadside inspections. Rob also reflects on the changing culture of drivers and the pressures of keeping good talent in an evolving industry.

This episode is packed with actionable advice for owner-operators stepping into fleet management as well as established carriers looking to sharpen their systems. If you are serious about growing a sustainable, reputable trucking business, Rob Carpenter’s strategies and stories will help you avoid painful mistakes and build a stronger foundation for the future.